EP0519406A2 - Nouveaux dérivés et perfluoropolyéthers, lubrifiants et supports d'enregistrement magnétique les utilisant - Google Patents

Nouveaux dérivés et perfluoropolyéthers, lubrifiants et supports d'enregistrement magnétique les utilisant Download PDF

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Publication number
EP0519406A2
EP0519406A2 EP92110161A EP92110161A EP0519406A2 EP 0519406 A2 EP0519406 A2 EP 0519406A2 EP 92110161 A EP92110161 A EP 92110161A EP 92110161 A EP92110161 A EP 92110161A EP 0519406 A2 EP0519406 A2 EP 0519406A2
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European Patent Office
Prior art keywords
perfluoropolyether
derivative
group
lubricant
amine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
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EP92110161A
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German (de)
English (en)
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EP0519406B1 (fr
EP0519406A3 (en
Inventor
Hirofumi c/o SONY MAGNETIC PRODUCTS INC. Kondo
Toshiharu c/o SONY MAGNETIC PRODUCTS INC Uchimi
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Sony Corp
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Sony Corp
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    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B5/00—Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
    • G11B5/62—Record carriers characterised by the selection of the material
    • G11B5/73—Base layers, i.e. all non-magnetic layers lying under a lowermost magnetic recording layer, e.g. including any non-magnetic layer in between a first magnetic recording layer and either an underlying substrate or a soft magnetic underlayer
    • G11B5/735—Base layers, i.e. all non-magnetic layers lying under a lowermost magnetic recording layer, e.g. including any non-magnetic layer in between a first magnetic recording layer and either an underlying substrate or a soft magnetic underlayer characterised by the back layer
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/38—Lubricating compositions characterised by the base-material being a macromolecular compound containing halogen
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B5/00—Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
    • G11B5/62—Record carriers characterised by the selection of the material
    • G11B5/68—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent
    • G11B5/70—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer
    • G11B5/71—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer characterised by the lubricant
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B5/00—Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
    • G11B5/62—Record carriers characterised by the selection of the material
    • G11B5/72—Protective coatings, e.g. anti-static or antifriction
    • G11B5/725—Protective coatings, e.g. anti-static or antifriction containing a lubricant, e.g. organic compounds
    • G11B5/7253—Fluorocarbon lubricant
    • G11B5/7257—Perfluoropolyether lubricant
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044—Acids; Salts or esters thereof
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
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    • C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
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    • C10M2213/06—Perfluoro polymers
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    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
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    • C10M2215/066—Arylene diamines
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    • C10M2215/067—Polyaryl amine alkanes
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    • C10M2215/226—Morpholines
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    • C10M2215/26—Amines
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    • C10N2040/16—Dielectric; Insulating oil or insulators
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    • C10N2040/17—Electric or magnetic purposes for electric contacts
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Definitions

  • This invention relates to novel perfluoropolyether derivatives.
  • the invention also relates to lubricants and magnetic recording mediums using such derivatives.
  • Magnetic recording mediums of the type which comprise a non-magnetic support and a magnetic layer formed on the support by vacuum deposition of a ferromagnetic metal have a very good smoothness on the surface of the magnetic layer. This leads to a substantial increase in contact area with a magnetic head and sliding members such as guide rollers, with the attendant problem that the coefficient of friction is increased and the magnetic layer is liable to be sticked over or attached intimately to such members, resulting in poor runnability and durability.
  • the lubricant which is successfully used in the magnetic recording medium should meet the following requirements.
  • novel perfluoropolyether derivatives are those compounds of the following formulas (1) to (4): wherein Rf represents a perfluoropolyether chain, and R1, R2, R3, and R4 independently represent a hydrogen atom or a hydrocarbon group having from 6 to 22 carbon atoms; wherein Rf represents a perfluoropolyether chain, and each R1, each R2, each R3, and each R4 independently represent a hydrogen atom or a hydrocarbon group having from 6 to 22 carbon atoms; wherein Rf represents a perfluoropolyether chain, R represents an alkylene group having from 2 to 18 carbon atoms or an aromatic group, and R5, R6, R7, R8, R9 and R10 independently represent a hydrogen atom or a hydrocarbon group having from 6 to 22 carbon atoms; and wherein Rf represents a perfluoropolyether chain, R represents an alkylene group having from 2 to 18 carbon atoms or an aromatic group, R5, R6, R7, R8, R9 and R10 independently represent
  • the lubricant according to the invention should comprise at least one of the perfluoropolyether derivatives of the formulas (1) to (4).
  • a magnetic recording medium which comprises a non-magnetic support, and a magnetic layer formed on the non-magnetic support.
  • a perfluoropolyether derivative of the general formula (1), (2), (3) or (4) is contained in the magnetic layer or is formed on the magnetic layer as a top coat.
  • the magnetic layer is made of a ferromagnetic metal.
  • the derivative is formed on the magnetic layer as a top coat.
  • the perfluoropolyether derivatives of the invention are reaction products between perfluoropolyethers having a carboxyl group at one or both ends and amines and also between perfluoropolyethers having a carboxyl group at one or both ends and diamines.
  • the derivative obtained from a perfluoropolyether having a carboxyl group at one end (which may be hereinafter referred to simply as monofunctional perfluoropolyether) and an amine is of the following general formula (1) wherein Rf represents a perfluoropolyether chain, and R1, R2, R3, and R4 independently represent a hydrogen atom or a hydrocarbon group having from 6 to 22 carbon atoms.
  • the derivative obtained from a perfluoropolyether having a carboxyl group at both ends (which may be hereinafter referred to simply as polyfunctional perfluoropolyether) and an amine is of the following general formula (2) wherein Rf represents a perfluoropolyether chain, and R1's, R2's, R3's and R4's may be the same or different and represent a hydrogen atom or a hydrocarbon group having from 6 to 22 carbon atoms.
  • the starting perfluoropolyethers may be ones which are commercially available.
  • Examples of the monofunctional polyether include F(CF2CF2CF2O) m CF2CF2COOH, CF3[OCF(CF3)CF2] j (OCF2) k COOH, wherein j and k are, respectively, an integer of 1 or over, and the like.
  • Examples of the polyfunctional perfluoropolyether include HOOCCF2(OCF2CF2) p (OCF2) q OCF2COOH, wherein p and q are, respectively, an integer of 1 or over, and the like.
  • these examples are shown only for illustration and useful perfluoropolyethers are not limited to those mentioned above.
  • the molecular weight of the perfluoropolyether is not critical and should preferably be in the range of from 600 to 5000, more preferably from 1000 to 4000. Too large a molecular weight of the perfluoropolyether is disadvantageous in that the end group or groups are less effective as an adsorption group. Further, the derivative obtained from such a large molecular weight perfluoropolyether becomes difficult to be dissolved in general-purpose solvents other than freons, e.g. ethanol. On the contrary, when the perfluoropolyether has too small a molecular weight, the lubricity based on the perfluoropolyether chain may be lost.
  • the amines include primary,secondary and tertiary amines. Quaternary ammonium compound may also be used.
  • the amine structure is not limitative and those amines having a branched structure, an isomeric structure and an alicyclic structure are usable. Also, the amines are not limitative with respect to the molecular weight and the presence or absence of unsaturated bond.
  • the amine should have an alkyl group or groups. More preferably, the alkyl group or groups have not less than 10 carbon atoms.
  • the derivatives may also be obtained from the monofunctional or polyfunctional perfluoropolyether and a diamine.
  • the derivative obtained from a monofunctional perfluoropolyether and a diamine is of the following general formula (3) wherein Rf represents a perfluoropolyether chain, R represents an alkylene group having from 2 to 18 carbon atoms or an aromatic group, and R5, R6, R7, R8, R9 and R10 independently represent a hydrogen atom or a hydrocarbon group having from 6 to 22 carbon atoms.
  • the derivative obtained from a polyfunctional perfluoropolyether and a diamine is of the following general formula (4) wherein Rf represents a perfluoropolyether chain, R represents an alkylene group having from 2 to 18 carbon atoms or an aromatic group, R5, R6, R7, R8, R9 and R10 independently represent a hydrogen atom or a hydrocarbon group having from 6 to 22 carbon atoms, and n is an integer of 1 or over.
  • the monofunctional and polyfunctional polyethers used in this case may be those set out with respect to the derivatives of the general formulas (1) and (2).
  • Known diamines may be used without limitation, including those diamines having a branched structure, an isomeric structure and an alicyclic structure irrespective of the molecular weight and the presence or absence of unsaturated bond.
  • Examples of the monoamines and diamines used to prepare the derivatives of the invention include aliphatic amines such as saturated monoamines,saturated diamines, alicyclic monoamines and alicyclic diamines, and aromatic amines.
  • saturated monoamines include: linear primary amines such as decylamine, undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, eicosylamine, docosylamine and the like; branched primary amines such as 2-dodecylamine, 3-dodecylamine, 4-dodecylamine, 5-dodecylamine, 6-dodecylamine, 2-decylamine, 3-decylamine, 4-decylamine, 5-dodecylamine and the like although not limited to those dodecylamines and decylamines; secondary symmetric amines such as didecylamine, diundecylamine, didodecylamine, ditridecylamine, ditetradec
  • symmetric amines such as tridecylamine, triundecylamine, tridodecylamine, tritridecylamine, tritetradecylamine, tripentadecylamine, trihexadecylamine, triheptadecylamine, trioctadecylamine, trieicosylamine, tridocosylamine and the like, and asymmetric amines such as dimethyldecylamine, dimethylundecylamine, dimethyldodecylamine, dimethyltridecylamine, dimethyltetradecylamine, dimethylpentadecylamine,dimethylhexadecylamine, dimethylheptadecylamine, dimethyloctadecylamine, dimethyleicosylamine, dimethyldocosylamine, butylmethyldecylamine, butylmethylundecylamine, butylmethyldodecylamine,
  • saturated diamines include: symmetric primary diamines such as ethylenediamine, propylenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, undecamethylenediamine, dodecamethylenediamine, tridecamethylenediamine, tetradecamethylenediamine, pentadecamethylenediamine, hexadecamethylenediamine, heptadecamethylenediamine, octadecamethylenediamine and the like; primary asymmetric diamines such as 1,2-dodecamethylenediamine, 1,3-dodecamethylenediamine, 1,4-dodecamethylenediamine, 1,5-dodecamethylenediamine, 1,6-dodecamethylenediamine, 1,7-dodecamethylenediamine, 2,3-dode
  • diamines having a terminal amino group such as N,N,N',N'-tetramethylethylenediamine, N,N,N',N'-tetramethylpropylenediamine, N,N,N',N'-tetramethyltetramethylenediamine, N,N,N',N'-tetramethylpentamethylenediamine, N,N,N',N'-tetramethylhexamethylenediamine, N,N,N',N'-tetramethylheptamethylenediamine, N,N,N',N'-tetramethyloctamethylenediamine, N,N,N',N'-tetramethylnonamethylenediamine, N,N,N',N'-tetramethyldecamethylenediamine, N,N,N',N'-tetramethylundecamethylenediamine, N,N,N',N'-tetramethyldodecamethylenediamine, N,N,
  • alicylic amines wherein an amino group is substituted at an alicyclic structure include alicyclic primary amines such as cyclopropylamine, cyclobutylamine, cyclopentylamine, cyclohexylamine, cyclooctylamine and the like, alicyclic secondary amines such as N-methylcyclopropylamine, N-methylcyclobutylamine, N-methylcyclopentylamine, N-methylcyclohexylamine, N-methylcyclooctylamine and the like, and alicyclic tertiary amines such as N,N-dimethylcyclopropylamine, N,N-dimethylcyclobutylamine, N,N-dimethylcyclopentylamine, N,N-dimethylcyclohexylamine, N,N-dimethylcyclooctylamine and the like.
  • the type of substituted alkyl group is limited to the methyl group
  • alicyclic diamines include alicyclic primary diamines such as cyclopropyldiamine, cyclobutyldiamine, cyclopentyldiamine, cyclohexyldiamine, cyclooctyldiamine and the like, alicyclic secondary diamines such as N-methylcyclopropyldiamine, N-methylcyclobutyldiamine, N-methylcyclopentyldiamine, N-methylcyclohexyldiamine, N-methylcyclooctyldiamine and the like, and alicyclic tertiary diamines such as N,N-dimethylcyclopropyldiamine, N,N-dimethylcyclobutyldiamine, N,N-dimethylcyclopentyldiamine, N,N-dimethylcyclohexyldiamine, N,N-dimethylcyclooctyldiamine and the like.
  • aromatic amines include alkylanilines such as N-methylaniline, N-ethylaniline, N-propylaniline, N-decylaniline, N-dodecylaniline, N-tetradecylaniline, N-hexadecylaniline, N-octadecylaniline and the like, symmetric tertiary anilines such as N,N-dimethylaniline, N,N-diethylaniline, N,N-dipropylaniline, N,N-didecylaniline, N,N-didodecylaniline, N,N-ditetradecylaniline, N,N-dioctadecylaniline and the like, and asymmetric tertiary amines such as ethylmethylaniline, propylmethylaniline, decylmethylaniline, dodecylmethylaniline, tetradecylmethylaniline,
  • alkyl moiety may be substituted and examples of such aniline derivatives include N-2-chloroethylaniline, N-2-bromoethylaniline, N-2-oxyethylaniline, N,N-2-dichloroethylaniline and the like.
  • derivatives of the aromatic diamines may be used including, for example, o-phenylenediamine, p-phenylenediamine, m-phenylenediamine and the like.
  • monoalkyl derivatives of the aromatic diamines may also be used including, for example, N-methylphenylenediamine, N-butylphenylenediamine, N-decylphenylenediamine, N-tetradecylphenylenediamine, N-octadecylphenylene diamine and the like.
  • dialkyl derivatives include N,N-dimethylphenylenediamine, N,N-ethylphenylenediamine, N,N-decylphenylenediamine, N,N-tetradecylphenylenediamine, N,N-hexadecylphenylenediamine, N,N-octadecylphenylenediamine and the like.
  • aromatic amines which have been illustrated above are those which have a benzene ring
  • other amine compounds having condensation-type polycyclic hydrocarbon structures which are substituted with an amino group or groups may also be used.
  • Such structures include, for example, pentalene, pyrene, indene, chrysene, naphthalene, naphthacene, azulene, heptalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, triphenylene, pleiadene, picene, perylene, pentaphene, pentacene, tetraphenylene, hexaphene, hexacene, rubicene, coronene, trinaphthylene, heptaphene, heptacen
  • amines having heterocyclic structures having a hetero atom in the molecule there may be used amines having heterocyclic structures having a hetero atom in the molecule.
  • those compounds having heterocyclic structures substituted with an amino group or groups may be used and examples of such heterocyclic structures include furan, thiophene, pyrrole, pyrroline, oxazole, iso-oxazole, thiazole, iso-thiazole, imidazole, imidazoline, imadazolidine, pyrazole, pyrazoline, pyrazolidine, furazane, pyran, pyridine,piperidine, pyridazine, pyrimidine, pyrazine, piperazine, morpholine, indole, indoline,indazole, chromene, chroman, iso-chroman, quinoline, iso-quinoline, cinnoline, phthalazine, quinazoline, quinoxaline
  • the perfluoropolyether derivatives of the invention may be those wherein the perfluoropolyether chain is partially hydrogenated. More particularly, not larger than 50% of the fluorine atoms of the perfluoropolyether chain may be substituted with a hydrogen atom.
  • a partially hydrogenated perfluoropolyether which is either monofunctional or polyfunctional in nature is used as the starting perfluoropolyether. By this, it becomes possible to reduce the amount of freon solvents for dissolution.
  • a typical example of a partially hydrogenated perfluoropolyether is shown below, but not limitative F(CF2CF2CF2O) a (CFHCF2CF2) b (CF2CF2CF2O) c CF2CF2COOH wherein a, b and c are, respectively, an integer of 1 or over.
  • novel perfluoropolyether derivatives can be simply prepared from perfluoropolyethers and amines or diamines according to the following procedure.
  • a monofunctional or polyfunctional perfluoropolyether and an amine or diamine are mixed and heated to a temperature higher than a melting point of the amine or diamine used, thereby obtaining an intended derivative. For instance, when stearylamine is used as the amine, it is sufficient to mix and heat the starting compounds at about 60°C.
  • the starting materials may be dissolved in organic solvents such as Freon, after which the solvent is removed, thereby obtaining an intended derivative.
  • organic solvents such as Freon
  • a metal salt of a perfluoropolyether such as a sodium salt and a quaternary ammonium salt is mixed and extracted with an organic solvent to obtain an intended derivative.
  • the quaternary ammonium salts may be chlorides, iodides, sulfates and the like.
  • the perfluoropolyether derivatives have good lubricity and can be utilized as a lubricant in wide fields. Especially, when the derivative is used as a lubrication for magnetic recording mediums, runnability, wear resistance and durability can be significantly improved, coupled with another advantage from the standpoint of fabrication of the medium that the derivative is dissolved in solvents other than freon, e.g. ethanol.
  • the perfluoropolyether derivatives may be used singly as a lubricant and may also be used in combination with other known lubricants.
  • the magnetic recording medium using the derivative lubricant is described.
  • the magnetic recording medium to which the invention is directed may be of the coating type which comprises a non-magnetic support and a magnetic layer formed on the support using a magnetic pain.
  • the non-magnetic support, and the magnetic powder and the resin binder used in the magnetic layer may be, respectively, made of materials ordinarily employed for this purpose.
  • non-magnetic supports examples include polymer supports made of plastic materials typical of which are polyesters, polyolefins, cellulose derivatives, vinyl resins, polyimide resins, polyamide resins, polycarbonate resins and the like, metallic substrates or sheets such as of aluminium alloys, titanium alloys and the like, ceramic and glass substrates such as alumina glass, and the like.
  • the support is not limitative with respect to the shape thereof and may be in the form of tapes, sheets, drums and the like.
  • the non-magnetic support may be formed with fine irregularities on the surfaces thereof in order to control surface properties.
  • magnétique powder examples include particles of ferromagnetic iron oxides such as ⁇ -Fe2O3, cobalt-deposited ⁇ -Fe2O3 and the like, ferromagnetic chromium dioxide, ferromagnetic metals, such as Fe, Co, Ni and the like, and alloys thereof, and fine particles of hexagonal ferrites.
  • the resin binders include polymers or copolymers of vinyl chloride, vinyl acetate, vinyl alcohol, vinylidene chloride, acrylic esters, methacrylic esters, styrene, butadiene, acrylonitrile and the like, polyurethane resins, epoxy resins, cellulose derivatives and the like.
  • the resin binders may be introduced with hydrophilic polar groups such as a carboxyl group, a sulfonate group, a sulfate group, a phosphate group or the like.
  • the derivative may be added to the magnetic layer or may be coated as a top coat on the surface of the magnetic layer.
  • both the addition to the magnetic layer and the top coating may be used in combination.
  • the amount of the perfluoropolyether derivative is not critical.
  • the derivative When internally added to the magnetic layer, the derivative is preferably used in an amount of from0.2 to 20 parts by weight per 100 parts by weight of the resin binder.
  • the derivative may be further applied, as a lubricant, to a metallic thin film-type magnetic recording medium wherein a continuous film of a ferromagnetic metal is formed as a magnetic layer on a non-magnetic support such as by sputtering.
  • the film structure of this type of medium is not limitative.
  • the derivative may be applied to a magnetic recording medium of the type wherein an undercoat is provided between the non-magnetic support and the magnetic layer or wherein a back coat layer is formed on a side of the support opposite to the magnetic layer.
  • the materials of the non-magnetic support and the metal magnetic thin film of this type of medium are not critical and hitherto known materials ordinarily used for this purpose may be used in the practice of the invention.
  • non-magnetic support may be those as used in the coating-type magnetic recording medium.
  • the substrate When a rigid substrate such as an Al alloy substrate or a glass sheet, the substrate may be subjected to alumite treatment to form an oxide film on the substrate surfaces or may be formed with a Ni-P film on the surfaces so as to harden the surface.
  • the metal magnetic thin film is formed as a continuous film by plating, sputtering or PVD techniques such as vacuum deposition.
  • a thin film include metal magnetic films for in-plane magnetization recording which are made of metals such as Fe, Co, Ni and the like, Co-pt alloys, Co-Pt-Ni alloys, Fe-Co alloys, Fe-Ni alloys, Fe-Co-Ni alloys, Fe-Ni-B alloys, Fe-Co-B alloys, Fe-Co-i-B alloys and the like, and Co-C alloy films.
  • an undercoat layer of a low melting non-magnetic material such as Bi, Sb, Pb, Sn, Ga, In, Ge, Si, Ti or the like is preliminarily formed on the non-magnetic support.
  • a metal magnetic material is vacuum deposited or sputtered from a vertical direction so that the low melting non-magnetic material is caused to be diffused into the magnetic thin film.
  • the thin film is prevented from orientation to ensure the in-plane isotropy and also to improve the coercive force.
  • the metal magnetic thin film may be formed on the surface thereof a hard protective film such as a carbon film, a diamond-like or amorphous carbon film, a chromium oxide film or a SiO2 film.
  • a hard protective film such as a carbon film, a diamond-like or amorphous carbon film, a chromium oxide film or a SiO2 film.
  • the derivative layer is formed as a top coat on the surface of the magnetic thin film or the protective film.
  • the amount of the perfluoropolyether derivative is preferably in the range of from 0.5 to 100 mg/m2, more preferably from 1 to 20 mg/m2.
  • the perfluoropolyether derivatives may be used singly as the lubricant for the medium or in combination with other known lubricants.
  • the derivative may be used in combination with an extreme pressure agent at a mixing ratio by weight of 30:70 to 70:30.
  • the extreme pressure agent When the extreme pressure agent is subjected to partial metallic contact in a boundary lubricating region, it reacts with the metallic surface owing to the heat of friction produced by the contact, so that a film of the reaction product is formed, thereby serving to mitigate the abrasion and wear of the metal.
  • the agent include phosphorus extreme pressure agents, sulfur extreme pressure agents, halogen extreme pressure agents, organometallic extreme pressure agents, composite extreme pressure agents and the like.
  • rust preventives may be added, if necessary.
  • Rust preventives may be ones which are ordinarily employed in these types of magnetic recording mediums and include, for example, phenols, naphthols, quinones, nitrogen-containing heterocyclic compounds, oxygen-containing heterocylic compounds, sulfur-containing heterocyclic compounds and the like.
  • the perfluoropolyether derivative may be internally added to or applied as a top coat onto the back coat layer as a lubricant.
  • the derivatives may be internally added to or applied as a top coat onto all or either of the magnetic coating layer or the metal magnetic thin film and the back coat layer in possible combinations.
  • the perfluoropolyether derivative when used as a lubricant, the derivative which has been prepared according to the procedure stated hereinbefore may not necessarily be used. More particularly, a starting perfluoropolyether and a starting amine or diamine may be mixed and used as a lubricant. By the mixing, the perfluoropolyether derivative is produced and exhibits lubricity.
  • the mixing ratio between the perfluoropolyether and the amine or diamine may be set at an equimolar ratio with respect to the carboxyl group and the amino group.
  • good lubricity is developed when the amine is used slightly in excess. This is considered for the following reason: when the mixture is applied onto a magnetic layer, the perfluoropolyether which exhibits acidity owing to its carboxyl groups is preferentially adsorbed on the surface of the basic ferromagnetic metallic thin film (magnetic layer), thus leading to the shortage of the amine.
  • the mixture when used as a lubricant of the magnetic recording medium, the mixture should has a ratio by mole between the amino group and the carboxyl group in the range of 3:7 to 40:1.
  • the amine salts or derivatives of perfluoropolyethers having a carboxyl group at one or both ends thereof exhibit good lubricity and can reduced a coefficient of friction.
  • the lubricity is scarcely impeded under severe conditions such as of low temperatures.
  • the derivative When using the derivative as the lubricant, the magnetic recording medium is significantly improved in runnability and durability.
  • the mixture was heated to 60°C and dissolved and was sufficiently agitated to obtain a uniform mixture, followed by cooling to obtain an amine salt of the perfluoropolyether.
  • Fig. 1 The IR absorption spectra of the thus obtained amine salt are shown in Fig. 1. From Fig. 1, it will be seen that the stretching vibration of NH at 3300 cm ⁇ 1 disappears and the absorption of the carbonyl at 1780 cm ⁇ 1 is shifted to 1670 cm ⁇ 1. There appear the stretching vibrations of CH at 2900 cm ⁇ 1 and 2825 cm ⁇ 1 and the stretching vibration of CF at from 1280 cm ⁇ 1 to 1060 cm ⁇ 1. From these facts, the structure of the resultant amine salt can be determined.
  • This example illustrates application to a metal thin film-type magnetic recording medium (vacuum deposited tape).
  • the product 1 in Table 1 was used to make the magnetic recording medium.
  • Co was deposited on a 14 ⁇ m thick polyethylene terephthalate film by an oblique vacuum deposition method to form a 200 nm thick ferromagnetic metal thin film. Subsequently, the product 1 of Table 1 was dissolved in a freon solvent and applied onto the surface of the thin film in an amount of 5 mg/m2, followed by cutting into 8 mm wide sample tapes.
  • Example 1 The general procedure of Example 1 was repeated using Product Nos. 2 to 14 instead of Product No. 1 in Table 1, thereby obtaining sample tapes.
  • the respective sample tapes were subjected to measurement of a coefficient of friction, still reproduction durability and shuttle durability under conditions of a temperature of 25°C and a relative humidity of 60%, a temperature of -5°C, and a temperature of 40°C and a relative humidity of 80%.
  • the still reproduction durability was evaluated as an attenuation time before the output was attenuated to -3dB under posing conditions.
  • the shuttle durability was evaluated as the number of shuttle cycles which were determined by subjecting the tape to a shuttle running of two minutes in one cycle until the output was lowered to 3 dB.
  • a blank tape which made no use of any lubricant and a tape which made use of only a perfluoropolyether terminated with a carboxyl group as a lubricant were also subjected to measurements. The results are shown in Tables 2 to 4.
  • Table 2 Conditions Coefficient Of Friction Still Reproduction Durability (minutes) Shuttle Durability (Cycles) Ex. 1 25°C, 60%R.H.
  • This example illustrates application to a coating-type magnetic recording medium.
  • Metallic magnetic powder 100 parts by weight Vinyl chloride-vinyl acetate copolymer 10.5 parts by weight
  • Polyurethane resin 10.5 parts by weight
  • Carbon (antistatic agent) 5 parts by weight
  • a fundamental composition of the above formulation provided, to which 1.5 parts by weight of Product No. 1 in Table 1 was added as a lubricant, followed by mixing in a ball mill for 24 hours and collection through a filter. 4 parts by weight of a curing agent was added to the mixture, followed by agitation for 30 minutes.
  • the resultant magnetic paint was applied onto a 12 ⁇ m thick polyethylene terephthalate base in a dry thickness of 5 ⁇ m, followed by magnetic orientation, drying and taking-up. The rolled film was calendered and cut into 1/2 inch wide sample tapes.
  • Example 15 The general procedure of Example 15 was repeated except that Product Nos. 2 to 14 were used instead of Product No. 1, thereby obtaining sample tapes.
  • the sample tapes were aged under conditions of a temperature of 25°C and a relative humidity of 60% and a temperature of 40°C and a relative humidity of 80% and subjected to measurements of a coefficient of friction and a stick-slip prior to and after the aging.
  • the results are shown in Tables 5 and 6.
  • the surface roughness was also determined since the roughness was considered as an index of a dispersion state, with results also shown in the tables.
  • Table 5 Conditions Prior To Aging After Aging Coefficient of Friction Stick-slip Coefficient Of Friction Stick-slip Ex.15 25°C, 60%R.H. 0.27 ⁇ 0.28 ⁇ 40°C, 80%R.H. 0.29 ⁇ 0.31 ⁇ Ex.16 25°C, 60%R.H.
  • the mixture was heated to 60°C and sufficiently agitated to make it uniform, followed by cooling to obtain an amine salt of the partially hydrogenated perfluoropolyether.
  • Co was deposited on a 14 ⁇ m thick polyethylene terephthalate by an oblique vacuum deposition method to form a 200 nm thick ferromagnetic metal thin film thereon.
  • a solution of each of Product Nos. 15 to 28 in a mixed solvent of Freon and ethanol was applied onto the surface of the metal magnetic thin film in an amount of 5 mg/m2, followed by cutting into 8 mm wide sample tapes.
  • the amine salts of the partially hydrogenated perfluoropolyethers are better than the partially hydrogenated perfluoropolyethers used singly with respect to the coefficient of friction, the still reproduction durability and the shuttle durability without degradation under various conditions.
  • This example illustrates mixing of a perfluoropolyether terminated with a carboxyl group and an alkylamine for use as a lubricant while varying the amount of the alkylamine.
  • lubricants having a perfluoropolyether mixed with the alkylamine at different weight ratios to the polyether of from 1/9 to 10/1, the perfluoropolyether alone (the above molar ratio being zero), and the alkylamine alone (the above molar ratio being infinite).
  • the perfluoropolyether used had the following formula, F(CF2CF2CF2O) m CF2CF2COOH, and the alkylamine used was of the formula, C18H37NH2.
  • Co was deposited on a 14 ⁇ m thick polyethylene terephthalate by an oblique vacuum deposition method to form a 200 nm thick ferromagnetic thin film.
  • the lubricants having different molar ratios, the perfluoropolyether and the alkylamine which were dissolved in Freon were each applied onto the thin film surface in an amount of 5 mg/m2, followed by cutting into 8 mm wide sample tapes.
  • Example 43 The general procedure of Example 43 was repeated except that the perfluoropolyether used had the following formula, [HOOC(CF2O) d (CF2CF2O) e CF2COOH] which have a carboxyl group at both ends and that the molar ratio was changed to a ratio between the amino group and the carboxyl group.
  • Table 12 Sample No. Stearylamine/Perfluoropolyether (by mole) Coefficient of Friction 25°C 60%R.H./40°C 80%R.H. 13 0 0.24/0.32 14 1/9 0.23/0.31 15 1/5 0.22/0.30 16 3/7 0.18/0.25 17 2/3 0.17/0.23 18 1/1 0.16/0.21 19 3/2 0.16/0.21 20 7/3 0.16/0.19 21 4/1 0.16/0.21 22 9/1 0.17/0.21 23 40/1 0.18/0.22 24 ⁇ 0.25/0.28
  • amines other than the stearylamine were not used. However, amines having linear, branched and alicyclic hydrocarbon groups or aromatic hydrocarbon groups are assumed to exhibit similar effects. The above is true of other perfluoropolyethers having a carboxyl group at one or both ends.
  • the mixture was heated to 60°C and sufficiently agitated to make a uniform solution, followed by cooling to obtain an amine salt of the perfluoropolyether having the carboxyl group at both ends.
  • Co was deposited on a 14 ⁇ m thick polyethylene terephthalate by an oblique vacuum deposition method to form a 200 nm thick ferromagnetic metal thin film thereon.
  • a solution of each of Product Nos. 29 to 37 in Table 13 in Freon was applied onto the surface of the metal magnetic thin film in an amount of 5 mg/m2, followed by cutting into 8 mm wide sample tapes.
  • the mixture was heated to 50°C and sufficiently agitated for uniformity, followed by cooling to obtain a diamine salt of the perfluoropolyether.
  • the IR absorption spectrum chart of the thus obtained amine salt is shown in Fig. 2. From the figure, it will be seen that the stretching vibration at 3300 cm ⁇ 1 disappears and a broad absorption of the quaternary amine appears at 3050 cm ⁇ 1 and that the absorption of the carbonyl at 1780 cm ⁇ is shifted to 1670 cm ⁇ 1 and there appear the stretching vibration of CH in the vicinity of 2950 cm ⁇ 1 and the stretching vibration of CF in a range of from 1350 cm ⁇ 1 and 1100 cm ⁇ 1. From these facts, the structure of the amine salt can be determined.
  • Co was deposited on a 14 ⁇ m thick polyethylene terephthalate by an oblique vacuum deposition method to form a 200 nm thick ferromagnetic metal thin film thereon.
  • a solution of each of Product Nos. 38 to 51 of Table 16 in a mixture of Freon and ethanol was applied onto the surface of the metal magnetic thin film in an amount of 5 mg/m2, followed by cutting into 8 mm wide sample tapes.
  • the diamine salts of the perfluoropolyethers are better than the perfluoropolyethers alone with respect to the coefficient of friction, the still reproduction durability and the shuttle durability and suffer little degradation under different severe conditions with very good results.
  • novel perfluoropolyether derivatives exhibit better lubricity than known perfluoropolyethers and that they are soluble in not only fluorinated hydrocarbons, but also other organic solvents, thus ensuring utilization of the derivatives in wide fields.
  • the magnetic recording medium using the perfluoropolyether derivatives as the lubricant can maintain good lubricity under various use conditions over a long term. Accordingly, there can be obtained the magnetic recording medium which has good runnability, wear resistance and durability.

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Lubricants (AREA)
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EP92110161A 1991-06-20 1992-06-16 Supports d'enregistrement magnétique utilisant lubrifiants à base de dérivés de polyéthers perfluoriques Expired - Lifetime EP0519406B1 (fr)

Applications Claiming Priority (12)

Application Number Priority Date Filing Date Title
JP14863791 1991-06-20
JP148637/91 1991-06-20
JP14863791 1991-06-20
JP16664091 1991-07-08
JP166640/91 1991-07-08
JP16664091 1991-07-08
JP19805391 1991-08-07
JP19805391 1991-08-07
JP198053/91 1991-08-07
JP35633091 1991-12-24
JP356330/91 1991-12-24
JP35633091A JP3240654B2 (ja) 1991-06-20 1991-12-24 パーフルオロポリエーテル誘導体及びこれを用いた潤滑剤並びに磁気記録媒体

Publications (3)

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EP0519406A2 true EP0519406A2 (fr) 1992-12-23
EP0519406A3 EP0519406A3 (en) 1993-04-28
EP0519406B1 EP0519406B1 (fr) 2000-10-25

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EP92110161A Expired - Lifetime EP0519406B1 (fr) 1991-06-20 1992-06-16 Supports d'enregistrement magnétique utilisant lubrifiants à base de dérivés de polyéthers perfluoriques

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US (2) US5453539A (fr)
EP (1) EP0519406B1 (fr)
JP (1) JP3240654B2 (fr)
DE (1) DE69231529T2 (fr)
IT (1) IT1254397B (fr)

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GB2286598A (en) * 1994-02-04 1995-08-23 Sony Corp Magnetic-head cleaning solution and magnetic head coated therewith
FR2724943A1 (fr) * 1994-09-28 1996-03-29 Sony Corp Lubrifiant pour un support d'enregistrement magnetique et support d'enregistrement magnetique
WO1998007145A1 (fr) * 1996-08-09 1998-02-19 Seagate Technology, Inc. Lubrifiants hydrosolubles, a base de polyether perfluore, pour couche de finition
US6093495A (en) * 1996-08-09 2000-07-25 Seagate Technology, Inc. Water soluble perfluoro polyether salt topcoat lubricants
US6558803B1 (en) 2000-07-03 2003-05-06 Adhesives Research Inc. Ambifunctional perfluorinated polyethers
KR100438253B1 (ko) * 1999-02-09 2004-07-02 시게이트 테크놀로지 엘엘씨 수용성 퍼플루오로 폴리에테르 톱코우트 윤활제
WO2010009191A2 (fr) * 2008-07-18 2010-01-21 3M Innovative Properties Company Composés d’éther fluorés et leurs procédés d’utilisation

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JPH0877541A (ja) * 1994-09-05 1996-03-22 Fuji Photo Film Co Ltd 磁気記録媒体
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US6761974B1 (en) 2001-05-04 2004-07-13 Seagate Technology Llc Polymeric lubricants with improved stability and thin film recording media comprising same
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US9315620B2 (en) 2011-08-02 2016-04-19 Solvay Specialty Polymers Italy S.P.A. (Per)fluoropolymer composition
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JP6042781B2 (ja) * 2013-08-21 2016-12-14 デクセリアルズ株式会社 潤滑剤及び磁気記録媒体
KR101944603B1 (ko) * 2014-09-03 2019-01-31 다이킨 고교 가부시키가이샤 방오성 물품
JP6437392B2 (ja) 2015-02-06 2018-12-12 デクセリアルズ株式会社 磁気記録媒体用潤滑剤、及び磁気記録媒体
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WO1995021209A1 (fr) * 1994-02-04 1995-08-10 Ao 'avtokoninvest' Amides et ethers d'acides perfluoropolyoxyalkylene sulfoniques ou perfluoropolyoxyalkylene carboxyliques et leur procede d'obtention
GB2286598A (en) * 1994-02-04 1995-08-23 Sony Corp Magnetic-head cleaning solution and magnetic head coated therewith
US5606098A (en) * 1994-02-04 1997-02-25 Ao "Avtokoninvest" Amides and esters of perfluoropolyoxaalkylene-sulfo- or perfluoropolyoxaalkylene-carboxylic acids and a process for producing same
GB2286598B (en) * 1994-02-04 1998-07-08 Sony Corp Magnetic head coated with magnetic-head cleaning solution
FR2724943A1 (fr) * 1994-09-28 1996-03-29 Sony Corp Lubrifiant pour un support d'enregistrement magnetique et support d'enregistrement magnetique
WO1998007145A1 (fr) * 1996-08-09 1998-02-19 Seagate Technology, Inc. Lubrifiants hydrosolubles, a base de polyether perfluore, pour couche de finition
US6093495A (en) * 1996-08-09 2000-07-25 Seagate Technology, Inc. Water soluble perfluoro polyether salt topcoat lubricants
KR100438253B1 (ko) * 1999-02-09 2004-07-02 시게이트 테크놀로지 엘엘씨 수용성 퍼플루오로 폴리에테르 톱코우트 윤활제
US6558803B1 (en) 2000-07-03 2003-05-06 Adhesives Research Inc. Ambifunctional perfluorinated polyethers
US6673397B2 (en) 2000-07-03 2004-01-06 Adhesives Research, Inc. Method of production of a crosslinked perfluorinated polyether release film
WO2010009191A2 (fr) * 2008-07-18 2010-01-21 3M Innovative Properties Company Composés d’éther fluorés et leurs procédés d’utilisation
WO2010009191A3 (fr) * 2008-07-18 2010-07-22 3M Innovative Properties Company Composés d’éther fluorés et leurs procédés d’utilisation

Also Published As

Publication number Publication date
IT1254397B (it) 1995-09-14
DE69231529T2 (de) 2001-05-17
JPH0593059A (ja) 1993-04-16
ITRM920471A1 (it) 1993-12-19
ITRM920471A0 (it) 1992-06-19
EP0519406B1 (fr) 2000-10-25
US5453539A (en) 1995-09-26
EP0519406A3 (en) 1993-04-28
JP3240654B2 (ja) 2001-12-17
DE69231529D1 (de) 2000-11-30
US5536425A (en) 1996-07-16

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